Toronto’s Thrilling October: Must-See Events and Happenings!

Toronto’s Thrilling October: Must-See Events and Happenings!

PumpkinFest at Downey’s Farm (Sept. 23 – Oct. 31)

Get ready for a pumpkin-packed adventure at Downey’s Farm! From wagon rides to a-maze-ing corn mazes, live entertainment, and adorable farm animals, they’ve got a fantastic lineup of family fun waiting for you.

LEGENDS OF HORROR (Sept. 29 – Oct. 31)

Prepare to be spooked and thrilled as Legends of Horror makes its chilling return to Casa Loma this October. Brace yourself for a hauntingly unforgettable experience!

Toronto Oktoberfest (OCTOBER 6 & 7)

Dust off your lederhosen and dirndls. Toronto’s favorite fall festival is back! Young and old, modern and traditional all blend together harmoniously in a relaxed and welcoming atmosphere at Toronto’s Oktoberfest!

Pumpkin Fest Toronto (October 6 – 9)

Enjoy a weekend filled with unlimited midway rides, inflatable fun, a sprawling pumpkin patch, local food trucks, live entertainment, tons of family photo ops, and so much more at Pumpkin Fest Toronto!

Woodbridge Fair (October 7-9)

Get ready for a fun-filled adventure at the Woodbridge Fair! From thrilling rides and games to captivating history and antiques, plus a mouthwatering array of fair foods and culinary arts, competitions with exciting prizes, and the wonders of animals and nature – this event has something for everyone to enjoy.

Planet in Focus (October 12 – 22)

Explore urgent environmental issues through captivating storytelling at the Planet in Focus International Environmental Film Festival, a Toronto-based not-for-profit organization.


Mark your calendars and prepare for an unforgettable cinematic experience at the 17th Annual Toronto After Dark Film Festival. As one of the most anticipated events in the city, this festival promises thrilling films, exciting premieres, and a celebration of the macabre and the fantastical that will leave you on the edge of your seat.

Next Stage Theatre Festival (October 18-29)

Experience the 16th Next Stage Theatre Festival at the historic Buddies in Bad Times Theatre, offering an experimental lineup of six productions with diverse artistic elements.

Art Toronto (October 26-29)

Art Toronto 2023 will return to downtown Toronto for a showcase of over 100 galleries from across Canada and abroad, attended by over 20,000 collectors, curators, and art enthusiasts.